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The SMTPS protocol uses port 465, not 587. Port 587 is instead used for STARTTLS. Helps getting administrators stuck in cryptic errors such as: Failed to send a testing email to "user@mydomain.com": could not initiate SMTP session: tls: first record does not look like a TLS handshake Reviewed-on: https://gitea.com/gitea/docs/pulls/295 Reviewed-by: Lunny Xiao <xiaolunwen@gmail.com> Co-authored-by: kairosys-dev <me@arch-on.top> Co-committed-by: kairosys-dev <me@arch-on.top>